Hydrochloric Acid → (RS)-1-[5-methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-2-ylmethyl]-4-(4-methyl-benzyl)-piperidin-4-ol

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Reaction Steps

(RS)-Toluene-4-sulfonic acid 5-methoxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-indol-2-ylmethyl ester (200 mg, 0.41 mmol) and 4-(4-methylbenzyl)-piperidin-4-ol (337 mg, 1.64 mmol) were heated in mesitylene (10 ml) for 20 hr at 140° C. After cooling 4N HCl was added to pHl and the mixture extracted with EtOAc (3×25 ml), the extracts dried (Na2SO4), filtered and evaporated. Purification of the crude material over SiO2 (Merck 230-400 mesh) eluting with EtOAc-cyclohexane-Et3N (9:10:1) afforded the title compound as a yellow oil (155.9 mg, 0.3 mmol, 73%), MS: m/e=521.4 (M+H+).

Provenance & Evidence